1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18426157, compound

HRID 279287Notes

Reaction equation

HRID 279287 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([NH:7][CH2:8][C:9]([OH:11])=O)=[O:6].CCN=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[Cl:39][C:40]1[CH:53]=[CH:52][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH2:48][CH:47]([NH2:51])[CH2:46]2)=[CH:42][CH:41]=1>C(Cl)(Cl)Cl.CCN(CC)CC>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH2:48][CH:47]([NH:51][C:9](=[O:11])[CH2:8][NH:7][C:5](=[O:6])[C:4]3[CH:12]=[CH:13][CH:14]=[C:2]([CH3:1])[CH:3]=3)[CH2:46]2)=[CH:52][CH:53]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 992233-Methylhippuric acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 18426178HCID 18426178, compound

Product 1

HCID 18426157HCID 18426157, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

N-(3-Methylbenzoyl)glycine (10.6 mg, 0.055 mmol), EDCI (10.5 mg) and 1-hydroxybenzotriazole hydrate (7.4 mg) were added to a solution of 1-(4-chlorobenzyl)-3-aminopiperidine dihydrochloride (14.9 mg, 0.050 mmol) and Et3N (15.2 mg) in CHCl3 (2.5 mL). The reaction mixture was stirred at 25° C. for 16 h, washed with 2 N aqueous NaOH (2 mL×2) and brine (1 mL). After filtration through PTFE membrane filter, the solvent was removed under reduced pressure to afford 1-(4-chlorobenzyl)-3-[{N-(3-methylbenzoyl)glycyl}amino]piperidine (compound No. 355) as a pale yellow oil (17.4 mg, 87%): The purity was determined by RPLC/MS (97%); ESI/MS m/e 400.0 (M++H, C22H26ClN3O2).

Workup

  1. washwashed with 2 N aqueous NaOH (2 mL×2) and brine (1 mL)
  2. filtrationAfter filtration through PTFE membrane
  3. filtrationfilter
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-011865d3e67c4cc18d2f83ce7846fade
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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